Synthesis of Enantiomerically Pure Nitronyl Nitroxide Radicals Through Chiral Pool

Title:Synthesis of Enantiomerically Pure Nitronyl Nitroxide Radicals Through Chiral Pool

Volume: 9 Issue: 5

Author(s): Xiang-Yang Qin, Yue Ma, Qiao-Feng Wang, Chao Wang, Xiao-Li Sun and Peng Liu

Affiliation:

Keywords: Chiral nitronyl nitroxides, N-Boc-D- or L- prolinol, chiral pool, superoxide, dismutase, radicals, cardiomyocytes, DNA, triphenylphosphine, azodicarboxylate

Abstract: Two pairs of new optically active nitronyl nitroxides derived from N-Boc-D- or L- prolinol are described. The synthetic route consist of (1) the synthesis of chiral aryl aldehydes by Mitsunobu reaction, (2) the condensation of the 2,3- bis(hydroxylamino)-2,3-dimethylbutane with chiral aldehydes to give 1,3-dihydroxyimidazolidine, and (3) the final oxidation of 1,3-dihydroxyimidazolidine with aqueous NaIO4 at 0 °C. These two pairs have been specifically designed for further assessing the differences in activity of chiral nitronyl nitroxides and for developing chiral molecular magnetic material by the metal-radical complexes approach.

Cite this article as:

Qin Xiang-Yang, Ma Yue, Wang Qiao-Feng, Wang Chao, Sun Xiao-Li and Liu Peng, Synthesis of Enantiomerically Pure Nitronyl Nitroxide Radicals Through Chiral Pool, Letters in Organic Chemistry 2012; 9 (5) . https://dx.doi.org/10.2174/157017812801264692